Potassium Carbonate → HCID 18594687, compound

HRID 328513Notes

Reaction equation

HRID 328513 reaction equation
C([O:4][C@@H:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][C@@H:8]1[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:11](=[O:23])[CH2:10][CH2:9]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>>[OH:4][C@@H:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][C@@H:8]1[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:11](=[O:23])[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 18594686HCID 18594686, compound

Product 1

HCID 18594687HCID 18594687, compound

Procedure

A solution of 2.26 g. of methyl 15(S)-acetoxy-9-oxo-prostanoate (Example 52) in 300 ml. of absolute alcohol containing 790 mg. of potassium carbonate is stired at ambient temperature for 72 hours then concentrated to near dryness under reduced pressure. The resulting mixture is extracted with ether. The combined extracts are washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 1.83 g. of an oil. Purfication by silica gel chromatography affords the suject compound as an oil; λ max. 2.92 (hydroxyl group), 5.74 μ (carbonyl groups); [αD25 -23° C. (0.2% in CHCl3).

Workup

  1. concentrationthen concentrated
  2. extractionThe resulting mixture is extracted with ether
  3. washThe combined extracts are washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customto give 1.83 g

Sources & evidence

ORD record
ord-ee9f5683b1a5413793abff181a4c0c7e
Source dataset
uspto-grants-1977_04
Patent number
US04017534

Reaction notes

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